--Generation--
by Lost-in-youu
Summary: Future-fic. "In life... some endings are bittersweet. Especially when it comes to love. Sometimes fate throws two lovers together only to rip them apart. Sometimes the hero finally makes the right choice but the timing is all wrong. And, as they say, timing is everything. Looks like this story might just have a second act. Let's hope it's not a tragedy." XOXO
1. 1-2-3

**1-2-3**

**Good Morning, Upper East Siders,**

** Welcome to the first day of senior year and the onset of a new social dynasty.**

**We heard that last night was a rough one. Well for two scoundrels in particular. Seems the Archibald's and the Bass' are things of legends. How are your heads, gentlemen? But a new term means a fresh start, and a new scandal on the horizon...**

**You know where to find me.**

**XOXO**

"Hurry _up_..! I don't have all day you know!" Cassandra banged on the bathroom door with her fist, trying to stir her pain-in-the-ass big brother from whatever hole he crawled in from last night. "Come on, Henry, get out of there!"

"It's no use." Emilia sighed from the hallway, watching her siblings antics with reservation, "you know he's probably still washing out the fumes from last night that have been caked into his scalp."

"What do _you_ know?" Cassandra fumed, banging on the door one final time, before shooting her younger sister and dirty look and flouncing off to find her mother. Emilia counted in her head _1-2-3..._ before right on cue, the bathroom door opened, where Henry emerged in a cloud of smoke looking around himself distrustfully.

"Has she gone?"

"You really shouldn't wind her up like that. You know it only makes her mad." Emilia walked over to Henry, took the cigarette out of his mouth and stubbed it out in the sink.

"Hey- I wasn't finished with that." Henry smirked cheekily, "and you know how I like to rile her up..." Emilia rolled her eyes and pushed her brother out of the bathroom. "I need to change." She said urgently, pulling her freshly washed uniform into the bathroom with her, along with a scattered pile of make up and accessories.

"_Ooooo... _Who's this for then? A certain boy that we might know?" Henry winked, leaning lazily against the door frame, his shirt hanging carelessly out of his trousers.

"Shut up, Henry!" Emilia laughed, her fair cheeks tinting with a soft, red blush.

It was then that the sound of heeled shoes could be heard upon the tiles, and Emilia darted into the bathroom and locked the door behind her. Henry leaned back against the wall and sighed, wishing that he last cigarette hadn't just been flushed down the drain. He tried quickly to brush down his messy, brown hair, to no avail, and was looking down at the floor, practising his best guilty look when he heard a-

"_Henry Charles Bass!_"

"Yes, mother." He replied, dragging his feet to where Blair Cornelia Bass was stood, her heels tapping furiously against the tiles. He noticed Cassandra smirking proudly behind her and maturely stuck his tongue out in response.

"It's your first day back at school, how can you already be in so much _trouble_?" She complained, leaning in to smell his alcoholic breath and noticing the rings beneath his eyes. She touched his messy hair with disappointment, trying to straighten out the effects of a wild pre-back to school party.

"What can I say, mother? I'm my father's son."

* * *

"I know... I got so totally wasted last night. You can't talk! Really? She ratted on you? Yeah I know she's _my_ girlfriend, but what do you expect me to do about it? God, man. I feel your pain. Yeah, sure. I'm just packing up some of my things now so I'll meet you out the front of St. Jude's in 30? Sure, see you later, Henry."

There was a knock on the door.

"I'm just about to head out to school, make it quick." Edmund replied, exasperated. Quickly throwing his school books into a rucksack and emptying piles of scrap paper all over his bed.

Into his son's bedroom stepped Nathaniel Archibald, quickly surveying the surroundings of his son's untidy room and looking at him with a serious gaze.

"It's about your sports scholarship, son. Look I know we've talked about this, but..."

Edmund sighed grumpily, "Look, Dad. I'll meet the scout, okay? I'll get it sorted, I just wanted this summer to relax, you know? Be young and carefree, you must remember those days?"

Nate looked ahead of him and smiled a little, but somehow carefree and Nate Archibald just didn't seem to fit in the same sentence. He had always felt the pressure of expectation, and wondered that Edmund didn't feel the same...

"Do you mean so you and Henry can go out and get drunk?" He raised his eyebrow, laughing at the irony of this parental speech given his ancient history with Henry's father.

"It's fine, Dad. It'll all be fine. Don't worry about it, okay? Just cheer up!" He laughed, swinging out of the door with a rucksack swung lightly across his back.

"Don't forget your brother!" Nate shouted, looking around his son's bedroom and wondering when he became _that_ guy. How he had ended up in_ this_ life? When had he become his _father..._

* * *

"This is a really, bad, idea." Dean gulped, standing on the edge of the sidewalk with his equally petrified sister as they gazed up at St Jude's School in front of them.

"I don't think Dad liked it either. But Mom insisted, it _is_ the best school in the area." Lucy added helpfully, clutching her books tighter to her chest. They stepped forward nervously, letting the yellow taxi cab shoot off behind them.

A group of boys around them began to point, the word _"Brooklynite" _stabbing it's way into their focus. Why would their father force them to go _here_? Dean ran his fingers through his short black hair and glanced back at his worried looking little sister, taking her hand as she looked up at him with her big, blue eyes.

"C'mon, Luce. We can do it together. 3-2-1..."

**We heard that two new Brooklynites are making their appearances at St Jude's today.**

**Arm yourselves newbies.**

**We're already preparing for your departure.**

**XOXO**

**Gossip Girl**

A/N: Thank you for reading! This is looking like it could end up being a big project! But I've got a huge family tree in mind, and hopefully a lot of scope for drama that could ensue following the next Generation teenagers... As long as I haven't bitten off more than I can chew!

This chapter could do with some major editing, but the idea is there. Let me know if you'd be interested in reading more and I'll try to carry it on for you guys :)

Please Rate and Review. It would mean the world 3

Love.


	2. Ancient History

**Ancient History**

**Good Morning, Upper East Siders,**

**We hear old habits die hard- and that seems to be the case for our very own Serena Archibald.**

**Seems she was spotted in a bookshop in Brooklyn first thing this morning. Now we all like a cliche, but doesn't this seem like history repeating itself?**

**XOXO**

"What are we going to do about him?" Blair sighed, stretching her arm across the kitchen counter and looking up at her husband sadly, who was drinking his morning coffee over a newspaper on the opposite side of the counter.

"Don't worry." He replied, without even looking up from his paper, "I'm sure he'll grow out of it," a sly smile sneaking its way across his lips.

"Well, not everyone has their very own Blair Waldorf." She smiled, creeping up behind him and wrapping her arms around his waist. "_Chuck..._" She teased innocently, planting a kiss on the back of his neck.

"What do you want?" Chuck raised his eyebrow, putting down the paper and waiting for his wife to offer him some kind of reward for his attention.

"Would you have a word with Henry? _Please?_" She asked soothingly, turning him around to face her as she wrapped a leg around his waist and laid her arms around his neck. She could feel him massaging her thigh beneath her skirt, and watched him drink in her scent with anticipation.

"You really think that'll work?" He questioned, leaning in towards her. His hot breath playing eagerly across her elegant cheekbones.

"I've heard..." She continued playfully, "that you can be very... _persuasive_..." as she leaned over to gently nibble his ear.

"You know, I'd do anything for you." He whispered huskily, swooping her up into his arms and setting her down on top of the counter.

Blair smiled victoriously, before looking at him hesitantly, "wait a minute, don't you have work?" She realised, catching a glimpse of the watch beneath his shirt sleeve.

"That's the advantage of being your own boss." He smirked cheekily, "I make the rules," catching her lips in an eager kiss and placing his body between her thighs.

She giggled happily, looking into his deep brown eyes before wrapping herself tighter around his waist.

_"We could never be boring..."_

And the world melted into dust around their feet.

* * *

Cassandra looked down from her view at the top of the Met steps and felt smugly satisfied watching all of the 'commoners' drifting around beneath her feet. With her head held high and her infamous beret seated firmly on top of her head, she could rule the world. Or St Jude's at least. Looking across at the two newbies stepping out of the taxi, she leaned over to her closest confederate, Sofia, whispering secretively and pointing with disgust at the new arrivals.

"What are _they_ doing here?" The Queen motioned, watching Sofia scrolling down the Gossip Girl. Her minions looking up at her expectantly, waiting for their commands.

"There's nothing about them on Gossip Girl," Sofia added, "Just that they're new to our school."

"Oh, not for long, honey. Not for long..." Cassandra murmured under her breath, watching the two students with a piercing gaze. The boy caught her glare, standing still for a second, watching her movements. He had pale skin, dark hair, and looked almost broody, in a quiet sort of way. He stared at her back, making Cassandra feel uncomfortable and flinch with revulsion.

"Eurgh, why is the new kid staring at me?" She motioned, patting her curls with her right hand and looking away disinterestedly.

"It's_ so_ rude..." Sofia nodded in agreement, offering Cassandra a mirror for her hair.

When Cassandra turned back round, the boy had started to walk off, and she watched him go with curiosity, his dark hair disappearing into the crowd of identical uniforms behind the school gates. Suddenly she couldn't see anything. The world had gone black as she felt someone's fingers lightly covering her eyes.

"Guess who?" A boyish voice uttered, leaving her world in darkness with his hands still in front of her face.

"Well of course I recognise my own boyfriend..." Cassandra smiled sweetly, turning around as she felt his hands lift so that she could finally gaze into the bright blue eyes of Edmund Archibald.

He was still looking a little hungover, but other than that, he was the perfect advertisement for Abercrombe and Fitch. His blonde hair swept back smoothly from his masculine jawline, and a soft, holiday tan covering his muscular body.

"Did you miss me?" He asked, pulling her into his arms.

"Of course I did." She smiled serenely, looking out across the busy school ground, "You're all I could ever wish for."

* * *

Dan looked around the shop with bewilderment, running his hands through his messy black hair as he noted the open volumes of dusty books covering every surface. How was he supposed to open up on time every morning with tacky school kids putting Fitzgerald in the fantasy section, and Austen novels on the shelves titled 20th Century... It was at times like these when he truly feared for modern education, especially with his two children attending St Jude's that very morning.

Walking over to the cash register, he looked again at the figures that he'd penciled down late yesterday evening. They certainly weren't promising, and with private schooling costs to worry about now the Humphrey's were struggling financially to make ends meet. Maybe he should have published that book that he wrote over a century ago after all.

"Hey." A familiar voice called from the doorway.

Dan looked up, into the eyes of the woman he had loved so long ago. Her wavy blonde hair covering her shoulders, her eyes still bright and sparkling, though there were aged frowns now present on her cheeks, and her shirt was a lot less revealing than he was used to. She'd buttoned up. He noticed. He imagined what he would look like to her after all this time, the struggling artist from long ago, the cynicism more pronounced after a lifetime of missed opportunities and bitter regrets.

"Hey yourself..." He replied nervously, disappearing under the counter to stack boxes and recover his embarrassment. He hadn't expected to see her. Ever again, in fact.

"I just... I hope you don't think it's weird..." Serena

"Why, would it be weird?" He joked with agitation, turning around to look her back in the eye. "My kids go to your school now, so it's probably best that we..."

"Well our kids were bound to meet. It's a small island." She remarked, looking at the floor a little as she spoke. "I just didn't want it to be awkward, you know, after..."

"No need to re-hash details of decades past." He snapped back firmly, taking the boxes over to the bookshelves to put some much needed space between them.

"Look, I came over here to be polite. So that if we did run into each other at parent teacher meetings then there wouldn't be any weirdness between us, but I can see that's just been a waste of time." Serena echoed fiercely, the tears stinging her eyes as she began to regret the decision to come here, clutching her bag nervously between her fingers.

"How's Nate?" He asked bitterly, not even meeting her eyes. Regretting his decision, he placed the final books on the shelf before saying "Serena, that was uncalled for, I'm sorry." His voice filled with regret, "I just missed you..." His tone breaking as he breathed the words quietly under his breath.

Looking up, the doorway to his bookshop was empty. She had already gone.

**With parents like these, ancient history runs in circles.**

**And yes, Cassandra Bass, we're looking at you. **

**You may have your very own prince charming, and your seat at the royal table, but it won't last long...**

**Do we smell trouble in paradise? **

**XOXO**

**Gossip Girl**

A/N: Thank you for reading! I'm hoping that the family dynamics and structures are beginning to look a little clearer. I didn't want to throw everything into the first chapter at once, but believe me, there's much more that I've got stashed up my sleeve for a rainy day!

Sorry for being slow on the update, but it's nearly Christmas... Please forgive me? 0:) I'll try to update them regularly as soon as I can!

Please Rate and Review. It would mean the world!

Love.


	3. Deals

**A new term. A fresh war. And looks like someone left the Basses on the rampage.**

**But what's this we see? A secret rendezvous in the courtyard, or just a casual encounter between friends?**

**Better make your mind up J, 'cause we're not sure that this little bird'll wait forever.**

**XOXO**

"Hi. James?" Emilia stumbled, clutching her books across her chest and walking over to where the young boy was sat underneath the shade, deep in the midst of an Orwell novel. He looked up and smiled sincerely, budging up to make room for her in the corner of the Constance Courtyard. It was a private spot,_ intimate_ almost. And it had made Emilia a bundle of nerves as she gathered the strength to smile back at him.

"Good book?" She asked with interest, peeking at the cover before making a horrified face. "It looks... depressing!" She laughed.

"I don't know," He smiled vaguely, "there's something about his gritty satire of our modern day consumerist society that I can relate to... Sometimes I just get so mad that I..." His frustration subsided as he looked into Emilia's forgiving expression and doe eyes as he continued, "I'm sorry, I must be boring you," laying the crumpled novel to rest at his feet.

"No!" Emilia persuaded, "please carry on. It's nice to listen to something other than underage boozing and parties at the moment." She nodded subtly at her brother and sister across the courtyard, Henry cattily eyeing up the new girls in short skirts ready for their first day, and Cassandra clearly making some poor girl's life a living hell using only bribery and blackmail through her mobile phone.

"I know _exactly_ how you feel." James replied, watching his brother, Edmund, casually laying an arm around the waist of Cassandra Bass.

"Are you two still not getting on?" She motioned with concern for her friend. She always found Edmund and James' relationship hard to fathom. There were no two brothers she knew who were such polar opposites. And it seemed both resented each other for it.

"Different interests... y'know? He's a sports guy, I'm a bookworm. He's dating the Queen of the School and I'm..."

"Sat here with me." Emilia finished, picking up her school books in a flurry and turning her head away from him. She knew that he would never like her as more than just a friend, yet still he managed to hurt her in a way that no-one else could. Her eyes cloudy, she stood up in a flash, and began to walk away.

He lightly grabbed her hand, "That's not what I meant, and you know it." He murmured, looking up at her. His messy, dark hair framing his innocent expression.

"I have class." She looked down, shuffling her toes in her pointed navy shoes and pretending to check her wristwatch.

"Still friends?" He asked, smiling heartily.

"Always." She smiled, turning away and walking across the courtyard, hiding her face so that no-one could see the tears rolling freely down her cheeks.

* * *

Serena rounded the doorway to her husband's office, tapping lightly on the glass as she saw his head in his hands, bent over his desk in frustration.

"Hey." She smiled weakly.

"Hey yourself," he nodded back, watching as she let herself into his office and shut the door. "So, what do I owe the pleasure of your company? I thought we gave up on indoor picnic lunches long ago..." There was a sadness in his eyes as he glanced at his wife. He knew that things hadn't been good between them. For a _long_ time. But saying it out loud... Seemed to open doors that neither one of them were quite ready to step through yet.

Serena looked hurt at the accusation, pulling out a couple of sandwiches from her bag and smiling awkwardly.

"Well whaddya' know?" Nate smiled, taking a sandwich from Serena's hand and smiling back at her with assurance.

Serena felt nervous. She was embarrassed to admit that she'd been to see Dan, but lying to her husband... _again_. Just put another obstacle between the one time golden couple of the Upper East Side.

"So why did you really come to see me? Be honest, Serena" Nate asked with concern, standing up from his desk chair and looking at the sadness in his wife's eyes. How had it got to this point? Where did it all start to go wrong?

"It's not serious." She smiled tensely, "I wanted to talk to you... About James."

"About James?" Nate questioned with confusion, "Why? What's he done?"

Serena looked into his bright blue eyes. Somewhere deep inside him she recognised the glimmer of adoration from long ago. She recognised the eyes that held her gaze, the fingers that wrapped themselves around her hands, and the soul that held her heart. She couldn't do it. She didn't want to hurt him. Not like this.

"That's the problem..." She sighed, "It's what he's not doing."

Nate looked lost, "Come again?"

"He's so quiet, and so _lonely_. And Edmund doesn't help with the cocky attitude he picked up from Henry. You two don't even really speak, properly. He just sits up in his room- pretending that the outside world doesn't exist. And it's not healthy for him. He needs his father. He needs to know that you care about him."

"Is that it?" Nate laughed, "You just wanted me to spend quality time with my son? Come here you..." He teased, pulling Serena onto his lap. "Why didn't you just say so. You made it seem like I was going off to a funeral or something!"

Serena buried her head in the crook of his shoulder, the weight of the world pressed against her as she tried to force a smile, kissing her husband appreciatively on the neck. He was good to her- far too good to her.

"I'll take James out first thing tomorrow morning, see if some morning coffee will liven our boy up. Are you sure that's it? There's nothing else on your mind?"

"No," Serena replied miserably. "That's everything."

* * *

Henry saw a rustle of light brown hair disappearing into the ladies bathroom, and for once, there was nothing sexually explicit on the menu as he rounded the corner to see his little sister wiping tear stains from her face in front of the mirror. Slowly, he watched as she pulled the braids from her hair, and the bow from her shirt collar, stuffing them back into her bag with shame.

"What are you doing?" He questioned urgently, coming up behind her and staring at her hollow expression in the reflection.

"I could ask you the same question!" Emilia cried, pushing his hands away and trying to force him out of the room before anyone saw him. "You do know that this is the _ladies_ room, right?"

"Yes, but more to the point, why are you removing the delicate accessories that you took so long preparing for this morning? Is it him? Is it James? 'Cause if he's hurt you I'll punch him, you know I will."

"Calm down, Henry." Emilia soothed, uncurling his fists and trying to relax the angered look on her protective brother's face. "He didn't do anything. We're friends."

"Well, you look radiant." He smiled, "and if he can't see how perfect you are then he's a fool."

Emilia smiled a little, looking awkwardly down at the floor. She always felt like the runt of the family around Cassandra and Henry. They both had such success with the opposite sex... Cassie with her trophy boyfriend, Edmund, and Henry with his... liaisons... But when James was around, she just felt like a weak little girl.

"You really think so?" She questioned nervously, looking for guidance in the experience of her much wiser brother.

"I know so. Now dry those eyes, you're not weak, Em. You're the most powerful woman I know." Henry smiled affectionately. It was a little know fact that Henry held any compassionate emotion, only his baby sister and his father even knew it existed: his father claiming that he only knew through first hand experience... _Yeah, right_. Chuck Bass was never _that_ cool.

"Oh, I'm sorry. I didn't realise the bathroom was occupied." A voice came from behind them. There was a girl stood by the door: her jet black hair and fringe framing her small face and bright blue eyes. "I'm new." She blushed nervously.

"Hi, I'm..."

"Leaving!" Emilia argued, pushing her brother and his leery expression out of the ladies room before he started on his next conquest.

"She's cute..." He whispered huskily, before finding himself on the other side of the bathroom door. The words "Call me!" Vaguely audible beyond the daily chatter of the school hallways.

"I'm _sorry_ about my brother..." Emilia sighed, looking at the new girl with sudden enthusiasm.

"_That_, was your brother?" The girl giggled, raising her eyebrows in a cheeky sort of way. She had originally been nervous about the prospect of a new school, with new faces to learn and none of her old friends. But in the comforting warmth of a new acquaintance she felt ready to take on anything that this school might throw at her.

"Don't get any ideas." She joked, "Henry doesn't _do_ relationships... What's your name, anyway?"

"Lucy." She smiled sweetly, "Lucy Humphrey."

"Sit together at lunch?" Emilia asked, thinking back to her alternative: a _friendly_ chat with James.

"Deal." Lucy replied.

* * *

"B? I need to talk to you... It's urgent. C'mon... I know you're there... Please pick up the phone. I really need my best friend right now, and..."

"Okay, okay! Quit your whining." Blair responded snappily, pulling her arm back through the sleeve of her dress and looking at a disheveled Chuck snoring quietly on the satin sheets beside her. "What's wrong?" She asked, feeling a little more concerned after the weight of sleep had lifted from her eyes.

"I need to tell you something, can you meet me?"

"Sure, sweetie. Central Park, our spot?"

"Deal."

Serena hung up, and Blair looked with anxiety at her screen. It was unlike Serena to be so terse, though she hadn't been her bright and radiant self for a while now. She knew that Serena and Nate had been having their problems... Maybe it was something to do with that? Looking reluctantly at Chuck's sleeping figure, she grabbed her purse, and tried to rearrange her messy brown locks into a semi-decent style before leaving the apartment.

** Spotted: An S & B heart to heart in Central Park**

**But with both ladies happily settled down, what could be their problems now?**

**Careful S... We see a storm on the horizon.**

**You know you love me**

**XOXO**

AN/: Firstly, I'm very sorry for such a long wait for any kind of new writing. Christmas was hard, but thankfully, we all got through it, and hopefully everything will be back to normal now. I'm not sure what I think of this chapter- I hope you like it? I'm sorry if I spent too much time focusing on Emilia (& the Archibald crisis!) but I thought they definitely deserved some airtime and I really wanted to draw on the relationship between Em and her big brother :) Please rate and review. I love to hear any kind of feedback! And yes- I did really try to make this chapter a bit longer, though it is 2.30am at this point, so I'm pretty tired... Goodnight guys :)


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